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Synthesis and photosynthetic electron transport inhibition of 2-substituted 6-fluorobenzothiazoles

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Abstract

Series of ten N-substituted 2-(aminoethyl)-6-fluorobenzothiazoles inhibited photosynthetic electron transport in spinach chloroplasts. The inhibitory activity linearly increased with hydrophobic contributions (expressed as hydrophobic constants π) and molar volumes of individual substituents in C(2) position of 6-fluorobenzothiazole scaffold to the optima π ca. 2 and MV ca. 233 cm3, while for more lipophilic and/or bulkier derivatives PET inhibiting activity linearly decreased. The site of inhibitory action of the tested compounds is situated on the donor side of photosystem II, and interaction of these compounds with aromatic amino acid residues in photosynthetic proteins was confirmed by fluorescence spectroscopy. Synthesis and characterization of five new Nα-(alkoxycarbonyl)-N-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-l-phenylalaninamides is presented as well.

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Acknowledgments

This study was supported by the Slovak Grant Agency VEGA 1/0612/11, by the Project APVV-0061-11, and by Sanofi-Aventis Pharma Slovakia. Authors also wish to acknowledge for the financial support to the Faculty of Chemistry, University of Pardubice.

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Authors and Affiliations

  1. Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Pardubice, Czech Republic

    Ales Imramovsky

  2. Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Bratislava, Slovakia

    Matus Pesko

  3. Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno, Czech Republic

    Josef Jampilek

  4. Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Bratislava, Slovakia

    Katarina Kralova

Authors
  1. Ales Imramovsky
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  2. Matus Pesko
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  3. Josef Jampilek
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  4. Katarina Kralova
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Correspondence to Ales Imramovsky or Josef Jampilek.

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Imramovsky, A., Pesko, M., Jampilek, J. et al. Synthesis and photosynthetic electron transport inhibition of 2-substituted 6-fluorobenzothiazoles. Monatsh Chem 145, 1817–1824 (2014). https://doi.org/10.1007/s00706-014-1283-9

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  • DOI: https://doi.org/10.1007/s00706-014-1283-9

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